Canrenone

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title: "Canrenone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["11β-hydroxylase-inhibitors", "21-hydroxylase-inhibitors", "antimineralocorticoids", "cholesterol-side-chain-cleavage-enzyme-inhibitors", "cyp17a1-inhibitors", "diuretics", "human-drug-metabolites", "lactones", "pregnanes", "progestogens", "spiro-compounds", "spirolactones", "spironolactone", "steroidal-antiandrogens", "world-anti-doping-agency-prohibited-substances", "conjugated-dienes", "enones"] description: "Chemical compound" topic_path: "general/11b-hydroxylase-inhibitors" source: "https://en.wikipedia.org/wiki/Canrenone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 460016527 | IUPAC_name = 10,13-Dimethylspiro[2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione | image = Canrenone.svg | image_class = skin-invert-image | alt = Skeletal formula of canrenone | image2 = Canrenone 3D ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of the canrenone molecule

| tradename = Contaren, Luvion, Phanurane, Spiroletan | Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | class = Antimineralocorticoid

| bioavailability = | protein_bound = 95% | metabolism = | elimination_half-life = 16.5 hours | excretion =

| CAS_number_Ref = | CAS_number = 976-71-6 | ATC_prefix = C03 | ATC_suffix = DA03 | PubChem = 13789 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 13192 | UNII_Ref = | UNII = 78O20X9J0U | ChEMBL_Ref = | ChEMBL = 1463345 | synonyms = Aldadiene; SC-9376; RP-11614; 7α-Desthioacetyl-δ6-spironolactone; 6,7-Dehydro-7α-desthioacetylspironolactone; 17-Hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid γ-lactone

| C=22 | H=28 | O=3 | SMILES = O=C5\C=C4\C=C/[C@@H]1C@H[C@@]4(C)CC5 | StdInChI_Ref = | StdInChI = 1S/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1 | StdInChIKey_Ref = | StdInChIKey = UJVLDDZCTMKXJK-WNHSNXHDSA-N

Canrenone, sold under the brand names Contaren, Luvion, Phanurane, and Spiroletan, is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone which is used as a diuretic in Europe, including in Italy and Belgium. It is also an important active metabolite of spironolactone, and partially accounts for its therapeutic effects.

Medical uses

Canrenone has been found to be effective in the treatment of hirsutism in women.

Heart failure

Two studies of canrenone in people with heart failure have shown a mortality benefit compared to placebo. In the evaluation which studied people with chronic heart failure (CHF), people that were treated with canrenone displayed a lower number of deaths compared to the placebo group, indicating a death and morbidity benefit of the medication.

One study compared 166 treated with canrenone to 336 given conventional therapy lasting 10 years. Differences in systolic and diastolic blood pressure was observed between both patient groups where, patients treated with canrenone, showed a lower blood pressure compared to conventional therapy. Uric acid was lower in the group treated with canrenone; however, no differences were seen in potassium, sodium, and brain natriuretic peptide (BNP) levels. Left ventricular mass was also lower in the group treated with canrenone and a greater progression of NYHA class was observed in the control group compared to patients treated with canrenone.

Another study concluded that treatment with canrenone in patients with chronic heart failure improves diastolic function and further decreased BNP levels.

Pharmacology

Pharmacodynamics

Canrenone is reportedly more potent as an antimineralocorticoid relative to spironolactone, but is considerably less potent and effective as an antiandrogen. Similarly to spironolactone, canrenone inhibits steroidogenic enzymes such as 11β-hydroxylase, cholesterol side-chain cleavage enzyme, 17α-hydroxylase, 17,20-lyase, and 21-hydroxylase, but once again, is comparatively less potent in doing so.

Pharmacokinetics

The elimination half-life of canrenone is about 16.5 hours.

As a metabolite

Canrenone is an active metabolite of spironolactone, canrenoic acid, and potassium canrenoate, and is considered to be partially responsible for their effects. It has been found to have approximately 10 to 25% of the potassium-sparing diuretic effect of spironolactone, whereas another metabolite, 7α-thiomethylspironolactone (7α-TMS), accounts for around 80% of the potassium-sparing effect of the drug.

History

Canrenone was described and characterized in 1959. It was introduced for medical use, in the form of potassium canrenoate (the potassium salt of canrenoic acid), by 1968.

Society and culture

Generic names

Canrenone is the and of the drug.

Brand names

Canrenone has been marketed under the brand names Contaren, Luvion, Phanurane, and Spiroletan, among others.

Availability

Canrenone appears to remain available only in Italy, although potassium canrenoate remains marketed in various other countries as well.

References

References

1. (April 1989). "Spironolactone metabolism: steady-state serum levels of the sulfur-containing metabolites". Journal of Clinical Pharmacology.
2. (6 December 2012). "Regulation of Aldosterone Biosynthesis: Physiological and Clinical Aspects". Springer Science & Business Media.
3. (1985). "Progestogens with antimineralocorticoid activity". Arzneimittel-Forschung.
4. (January 1983). "The interaction of canrenone with oestrogen and progesterone receptors in human uterine cytosol". British Journal of Clinical Pharmacology.
5. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
6. (23 May 1991). "Dictionary of Steroids". CRC Press.
7. (May 2004). "Cross reactivity due to positive canrenone interference". Gut.
8. (January 2000). "Index Nominum 2000: International Drug Directory". Taylor & Francis.
9. (1989). "Effectiveness of short term canrenone treatment in idiopathic hirsutism". Minerva Endocrinologica.
10. (March 2019). "Canrenone on cardiovascular mortality in congestive heart failure: CanrenOne eFFects on cardiovascular mortality in patiEnts with congEstIve hearT failure: The COFFEE-IT study". Pharmacological Research.
11. (October 2011). "Effect of canrenone on left ventricular mechanics in patients with mild systolic heart failure and metabolic syndrome: the AREA-in-CHF study". Nutrition, Metabolism, and Cardiovascular Diseases.
12. (15 December 1990). "Chronic Hyperandrogenic Anovulation". CRC Press.
13. (23 September 1997). "Diuretic Agents: Clinical Physiology and Pharmacology". Academic Press.
14. (April 1981). "Chemical suppression of steroidogenesis". Environmental Health Perspectives.
15. (15 December 2011). "Pharmacology". Lippincott Williams & Wilkins.
16. (15 April 2008). "Ascites and Renal Dysfunction in Liver Disease: Pathogenesis, Diagnosis, and Treatment". John Wiley & Sons.
17. (September 2008). "Mineralocorticoid receptor antagonists and endothelial function". Current Opinion in Investigational Drugs.
18. (2001). "Some Thyrotropic Agents". World Health Organization.
19. (January 2013). "A safe and practical method for the preparation of 7α-thioether and thioester derivatives of spironolactone". Steroids.
20. William Andrew Publishing. (22 October 2013). "Pharmaceutical Manufacturing Encyclopedia, 3rd Edition". Elsevier.
21. "List of Aldosterone receptor antagonists". Drugs.com.
22. "Potassium Uses, Side Effects & Interactions". Drugs.com.

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